反応 #64644

反応方程式

2,3-Dihydro-2-oxo-1-phenyl-3-(4-pyridinylmethyl)-1H-indole-3-butanoic acid ethyl ester hydrochloride

borane

MeOH

→

1,3-Dihydro-3-(4-hydroxybutyl)-1-phenyl-3-(4-pyridinylmethyl)-2H-indol-2-one Hydrochloride

溶媒

THF

THF

反応条件

後処理

1. 1
   濃縮the mixture was concentrated in vacuo
2. 2
   workup.WAITThe residue was digested with 100 ml 1N HCl for 3 hours at 80° C.
3. 3
   濃縮the solution was concentrated
4. 4
   その他The residue was partitioned between 200 ml EtOAc and 100 ml 5% NaHCO3
5. 5
   洗浄The organic phase was washed with water and brine
6. 6
   乾燥dried over MgSO4
7. 7
   ろ過filtered
8. 8
   workup.ADDITIONtreated with 44 ml 1N HCl-Et2O
9. 9
   その他evaporated in vacuo
10. 10
    workup.WAITleft
11. 11
    workup.WAITstanding overnight
12. 12
    ろ過The resulting crystals were collected by filtration
13. 13
    洗浄washed with Et2O
14. 14
    その他dried
15. 15
    その他to give the product in 30% (2.72 g)
16. 16
    その他yield

実験手順

A suspension of 2,3-Dihydro-2-oxo-1-phenyl-3-(4-pyridinylmethyl)-1H-indole-3-butanoic acid ethyl ester hydrochloride (10.0 g, 22.2 mmol) in 50 ml dry THF was treated with excess 1M BH3 -THF and stirred at room temperature for 3 days. The excess borane was decomposed with MeOH, and the mixture was concentrated in vacuo. The residue was digested with 100 ml 1N HCl for 3 hours at 80° C. , and the solution was concentrated. The residue was partitioned between 200 ml EtOAc and 100 ml 5% NaHCO3. The organic phase was washed with water and brine, dried over MgSO4, filtered, treated with 44 ml 1N HCl-Et2O, evaporated in vacuo. The residue was suspended in hot CH3CN and left standing overnight. The resulting crystals were collected by filtration, washed with Et2O, and dried to give the product in 30% (2.72 g) yield; mp 196°-197° C.; IR(nujol): OH @3356 cm-1 ; C=O @1709 cm -1 ; NMR(CDCl3TMS): δ1.13, 1.24 (2m, 2H, CH2 --C--CO), 2.51 (m, 2H, CH2 --CO), 2.1-3.0 (m, 2H, CH2 --C--C--CO), [3.40 (d, 1H, J=12.4 Hz), 3.54 (d, 1H, J=12.5 Hz), CH2 -Pyr], 3.48 (t, 2H, OCH2), [6.5 (m, 1H), 7.2 (m, 2H), 7.4 (m, 6H), Phe+1,2-Phe], [6.99 (d, 2H), 8.49 (d, 2H), 4-Pyr]; mass spec m/e 373(M+1); Anal calcd for C24H24N2O2HCl, MW 408.93: C, 70.49; H, 6.16; N, 6.85. Found: C, 70.44; H, 6.00; N, 6.67.

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